The present invention relates to derivatives of 1-acetyl-3,3-dimethylcyclohexane having the generic structure: ##STR2## wherein one of the dashed lines is a carbon-carbon single bond or a carbon-carbon double bond and the other of the dashed lines is a carbon-carbon single bond and R is hydrogen or methyl, produced by the novel process of our invention and novel compositions using one or more of such 1-acetyl-3,3-dimethylcyclohexane derivatives to augment or enhance the flavor and/or aroma of consumable materials or impart flavor and/or to consumable materials.
There has been considerable work performed relating to substances which can be used to impart (modify, augment or enhance) flavors and fragrances to (or in) various consumable materials. These substances are used to diminish the use of natural materials, some of which may be in short supply and to provide more uniform properties in the finished product. Sweet, fruity, raspberry, woody, lemon, piney, ionone-like, blueberry and floral aroma characteristics and sweet, raspberry, lemony, sweet fruity, red berry, piney, floral, ionone-like and nut meat flavor characteristics are particularly desirable for many uses in foodstuff flavorings, chewing gum flavors, toothpaste flavors and medicinal product flavors.
Fruity, woody, piney aromas with armoise and floral nuances and slight chocolate undertones are desirable in several types of perfume compositions, perfumed articles and colognes.
Acetylcyclohexane and 1-acetyl-3,3-dimethylcyclohexane are known substituents in perfumery. Thus, Arctander, "Perfume and Flavor Chemicals (Aroma Chemicals)", published in 1969, discloses acetylcyclohexane in Volume I, number 36:
"Peculiar camphoraceous-sweet odor with a certain amount of floral tones.
"Although this chemical would primarily lend itself to perfume compositions in the Pine, Wood, Herbaceous and other non-floral types, it has a similarity to the harsh-floral types such as Hyacinth, etc. and its sweetness is sometimes classified as `musky`. "
1-Acetyl-3,3-dimethylcyclohexane is disclosed as a fragrance material in U.S. Pat. No. 3,487,102, issued on Dec. 30, 1969.
The fragrance properties of the aforementioned acetyldimethylcyclohexane derivatives are different in kind from the fragrance properties of the compounds of the instant invention.
Firmenich's Dutch published application No. 7500838 discloses the preparation of the compound having the structure: ##STR3## and discloses its use in perfumery and in augmenting foodstuff flavors. The perfumery use of this compound and other members of its class as "floral, green, herbaceous and chypre" useful in galbanum resinoids is also disclosed.
The compounds disclosed in Dutch published application No. 7500838 have organoleptic properties which causes them to be different in kind from the 1acetyl-3,3-dimethylcyclohexane derivatives of our invention, which have unobvious, unexpected and advantageous characteristics in the field of augmenting or enhancing the organoleptic impressions of foodstuffs, foodstuff flavors, perfumes, perfumed articles and medicinal products.